Amino Acid Derivatives of Chlorin-e<sub>6</sub>—A Review
Details of the structural elucidation of the clinically useful photodynamic therapy sensitizer NPe6 (<b>15</b>) are presented. NPe6, also designated as Laserphyrin, Talaporfin, and LS-11, is a second-generation photosensitizer derived from chlorophyll-a, currently used in Japan for the t...
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| Format: | Article |
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MDPI AG
2023-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/8/3479 |
| _version_ | 1797604070108692480 |
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| author | Maria da Graça H. Vicente Kevin M. Smith |
| author_facet | Maria da Graça H. Vicente Kevin M. Smith |
| author_sort | Maria da Graça H. Vicente |
| collection | DOAJ |
| description | Details of the structural elucidation of the clinically useful photodynamic therapy sensitizer NPe6 (<b>15</b>) are presented. NPe6, also designated as Laserphyrin, Talaporfin, and LS-11, is a second-generation photosensitizer derived from chlorophyll-a, currently used in Japan for the treatment of human lung, esophageal, and brain cancers. After the initial misidentification of the structure of this chlorin-e<sub>6</sub> aspartic acid conjugate as (<b>13</b>), NMR and other synthetic procedures described herein arrived at the correct structure (<b>15</b>), confirmed using single crystal X-ray crystallography. Interesting new features of chlorin-e<sub>6</sub> chemistry (including the intramolecular formation of an anhydride (<b>24</b>)) are reported, allowing chemists to regioselectively conjugate amino acids to each available carboxylic acid on positions 13<sup>1</sup> (formic), 15<sup>2</sup> (acetic), and 17<sup>3</sup> (propionic) of chlorin e<sub>6</sub> (<b>14</b>). Cellular investigations of several amino acid conjugates of chlorin-e<sub>6</sub> revealed that the 13<sup>1</sup>-aspartylchlorin-e<sub>6</sub> derivative is more phototoxic than its 15<sup>2</sup>- and 17<sup>3</sup>-regioisomers, in part due to its nearly linear molecular conformation. |
| first_indexed | 2024-03-11T04:41:04Z |
| format | Article |
| id | doaj.art-0bc0c4c91f644b98a2d9e929a098be7e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T04:41:04Z |
| publishDate | 2023-04-01 |
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| series | Molecules |
| spelling | doaj.art-0bc0c4c91f644b98a2d9e929a098be7e2023-11-17T20:39:34ZengMDPI AGMolecules1420-30492023-04-01288347910.3390/molecules28083479Amino Acid Derivatives of Chlorin-e<sub>6</sub>—A ReviewMaria da Graça H. Vicente0Kevin M. Smith1Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USADepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USADetails of the structural elucidation of the clinically useful photodynamic therapy sensitizer NPe6 (<b>15</b>) are presented. NPe6, also designated as Laserphyrin, Talaporfin, and LS-11, is a second-generation photosensitizer derived from chlorophyll-a, currently used in Japan for the treatment of human lung, esophageal, and brain cancers. After the initial misidentification of the structure of this chlorin-e<sub>6</sub> aspartic acid conjugate as (<b>13</b>), NMR and other synthetic procedures described herein arrived at the correct structure (<b>15</b>), confirmed using single crystal X-ray crystallography. Interesting new features of chlorin-e<sub>6</sub> chemistry (including the intramolecular formation of an anhydride (<b>24</b>)) are reported, allowing chemists to regioselectively conjugate amino acids to each available carboxylic acid on positions 13<sup>1</sup> (formic), 15<sup>2</sup> (acetic), and 17<sup>3</sup> (propionic) of chlorin e<sub>6</sub> (<b>14</b>). Cellular investigations of several amino acid conjugates of chlorin-e<sub>6</sub> revealed that the 13<sup>1</sup>-aspartylchlorin-e<sub>6</sub> derivative is more phototoxic than its 15<sup>2</sup>- and 17<sup>3</sup>-regioisomers, in part due to its nearly linear molecular conformation.https://www.mdpi.com/1420-3049/28/8/3479chlorin-e<sub>6</sub>amino acid conjugatephotodynamic therapyNPe6TalaporfinLS-11 |
| spellingShingle | Maria da Graça H. Vicente Kevin M. Smith Amino Acid Derivatives of Chlorin-e<sub>6</sub>—A Review Molecules chlorin-e<sub>6</sub> amino acid conjugate photodynamic therapy NPe6 Talaporfin LS-11 |
| title | Amino Acid Derivatives of Chlorin-e<sub>6</sub>—A Review |
| title_full | Amino Acid Derivatives of Chlorin-e<sub>6</sub>—A Review |
| title_fullStr | Amino Acid Derivatives of Chlorin-e<sub>6</sub>—A Review |
| title_full_unstemmed | Amino Acid Derivatives of Chlorin-e<sub>6</sub>—A Review |
| title_short | Amino Acid Derivatives of Chlorin-e<sub>6</sub>—A Review |
| title_sort | amino acid derivatives of chlorin e sub 6 sub a review |
| topic | chlorin-e<sub>6</sub> amino acid conjugate photodynamic therapy NPe6 Talaporfin LS-11 |
| url | https://www.mdpi.com/1420-3049/28/8/3479 |
| work_keys_str_mv | AT mariadagracahvicente aminoacidderivativesofchlorinesub6subareview AT kevinmsmith aminoacidderivativesofchlorinesub6subareview |